Phenethylamine → 2-Chloro-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

HRID 2268426Notes

Reaction equation

HRID 2268426 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:13](Cl)[N:12]=1.C(N(CC)CC)C>C(#N)C>[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[C:13]([NH:9][CH2:1][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

Participants

5

Reactant 3

HCID 1001Phenethylamine2×HCID 8471TriethylamineHCID 2702652,6-Dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Product 1

HCID 207091842-Chloro-N-phenethyl-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amineYield 94.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phenethylamine (7.0 g, 58.4 mmol) was added to a stirred solution of 2,6-dichloro-9-tetrahydro-2H-pyran-2-yl-9H-purine (14.5 g, 53.1 mmol) (preparation 5) and triethylamine (21 g, 212.5 mmol) in acetonitrile (200 ml). The reaction mixture was stirred for 3 hr at room temperature and then more phenethylamine (1 g, 8.3 mmol) was added. The reaction mixture was stirred for a further 1 hr and then the solvent was removed under reduced pressure to give a residue which was partitioned between diethyl ether (500 ml) and water (250 ml). The diethyl ether layer was washed with more water (300 ml). The solvent was removed from the organic phase under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with diethyl ether to give the title compound (17.9 g) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for a further 1 hr
  2. customthe solvent was removed under reduced pressure
  3. customto give a residue which
  4. customwas partitioned between diethyl ether (500 ml) and water (250 ml)
  5. washThe diethyl ether layer was washed with more water (300 ml)
  6. customThe solvent was removed from the organic phase under reduced pressure
  7. customto give a residue which
  8. customwas purified by column chromatography on silica gel eluting with diethyl ether

Sources & evidence

ORD record
ord-99eef421966e48dd9a07c4e058c35935
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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